JPS6331463B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention provides novel N,N'-bis(trifluoromethylsulfonyl)oxamide compounds, superior compositions containing the compounds useful for generating chemiluminescence upon reaction with hydrogen peroxide, and superior compositions therewith. The present invention relates to a method of generating chemiluminescence by reacting the composition, which has excellent properties. The prior art has shown that oxamides give chemiluminescence when reacted under certain conditions (Rauhut et al., US Pat. No. 3,442,815).
and Maulding, U.S. Pat. No. 3,400,080).
While the oxamides disclosed to date provide substantially high light intensities, the efficiency of the system is 1% or less, as measured by chemiluminescent quantum yield. Therefore, there is a need for compositions that provide superior light intensity over extended periods of time and have chemiluminescent quantum yields greater than 1%. According to the present invention, the following formula () In the formula, R and R' are independently a C1-C6 alkyl group substituted with a C1-C6 alkoxy group, a phenyl group substituted with a substituent selected from the group consisting of halo and nitro, or a halo Provided are novel compounds represented by: which is a pyridyl group substituted with . According to the invention, (a) a compound of formula () as previously defined which reacts with a peroxide component to generate chemiluminescence; (b) an organic fluorescent compound; and (c) dilution. Also provided are compositions comprising the following components, wherein these components are present in sufficient proportions and concentrations to generate chemiluminescence when reacted with the peroxide component. According to the invention there is also provided a method for generating chemiluminescence, which comprises reacting the above composition with a peroxide component. The chemiluminescent composition of the novel compound of formula () is
Emergency lighting device for home use, on the road, in coal mines, on life jackets, and on diagonal evacuation ditches of aircraft (U.S. Patent No.
3800132)). The compounds of the invention can be used to provide long-lasting chemiluminescence. These things are
The oxamides of U.S. Pat. Nos. 3,400,080 and 3,442,815 are superior in that they provide superior chemiluminescent quantum yields of about 10 to 35%, compared to about 1% or less for prior art oxamides. It stands out in particular. The compounds of the present invention can be prepared by reacting about 2:2 molar ratios of the appropriate trifluoromethanesulfonamide or trifluoromethanesulfonanilide with oxalyl chloride in the presence of an acid binder by methods known in the state of the art. Easily manufactured. Trifluoromethanesulfonanilide and N
-Methods for the preparation of substituted trifluoromethanesulfonamides are known in the state of the art (Harrington et al.
US Patent No. 3558698; US Patent No. 3629332; US Patent No. 3799968
No. 3865844; No. 3897449; No. 3920444;
and Moore et al., US Pat. No. 3,609,187). Examples of compounds of formula () include: N,N'-bis(4-chlorophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2-bromophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(4-fluorophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(3-iodophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,4-dichlorophenyl)-
N,N'-bis(trifluoromethylsulfonyl)
Oxamide, N,N'-bis(2,4-dibromophenyl)-
N,N'-bis(trifluoromethylsulfonyl)
Oxamide, N,N'-bis(2,5-difluorophenyl)
-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(4-bromo-2-chlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'- Bis(2-chloro-4-fluorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,4,5-trichlorophenyl)-N,N'- Bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,4,6-trichlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(3, 4,5-Trichlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,4-dichloro-6-fluorophenyl)-N,N'-bis( trifluoromethylsulfonyl)oxamide, N,N'-bis(2,6-dichloro-4-fluorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2, 3,5,6-tetrachlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,3,4,5,6-pentafluorophenyl)-N, N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(4-nitrophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,4-dinitrophenyl)-
N,N'-bis(trifluoromethylsulfonyl)
Oxamide, N,N'-bis(4-chloro-2-nitrophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(4-fluoro-3-nitrophenyl)-N, N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,5-dichloro-4-nitrophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis (2,6-dichloro-4-nitrophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2-methoxyethyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2-chloro-3-pyridyl)-
N,N'-bis(trifluoromethylsulfonyl)
Oxamide, preferred compounds are as follows: N,N'-bis(2,4-dichlorophenyl)-
N,N'-bis(trifluoromethylsulfonyl)
Oxamide, N,N'-bis(2,4,5-trichlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2,4,6-trichlorophenyl) )-N,N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(4-nitrophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2-methoxyethyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(4-chlorophenyl)-N,
N'-bis(trifluoromethylsulfonyl)oxamide, N,N'-bis(2-chloro-3-pyridyl)-
N,N'-bis(trifluoromethylsulfonyl)
Oxamide. A particularly preferred compound is N,N'-bis(2,4,
5-trichlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. As used herein, the term "chemiluminescence" refers to the luminescence of approximately 300 and 1200 nanometers (nm) due to chemical reactions.
shall be defined as the occurrence of electromagnetic radiation during As used herein, the phrase "a composition that reacts with a peroxide component to generate chemiluminescence" refers to a composition in a diluent at a concentration sufficient to generate chemiluminescence when combined with a peroxide component. It is defined as a mixture of the compound () and a fluorescent compound. Thus, the initial concentrations of the components of formula (), the fluorescent compound, and the peroxide component in the reaction mixture must be sufficient to generate chemiluminescence. The fluorescent compounds contemplated herein can be broadly defined as those that do not readily react with the peroxide component or compound of formula () used in the present invention. Typical fluorescent compounds for use in the present invention have an emission spectrum between 300 and 1200 nanometers;
A compound that is at least partially soluble in the diluent used. Among these are conjugated polycyclic aromatic compounds having at least three fused rings, such as: anthracene, substituted anthracene, benzanthracene, phenanthrene, substituted phenanthrene, naphthacene, substituted naphthacene, pentacene, Substituted pentacene, perylene, substituted perylene, violanthrone, substituted violanthrone, etc. Typical substituents for all of these are phenyl, lower alkyl, chlorine, bromine, cyano, alkoxy (1 to 16 carbon atoms), and other similar substituents that do not interfere with the photogenerated reactions contemplated here. It is. Numerous other fluorescent compounds having the properties indicated above are well known in the state of the art. Many of these are referred to in Peter Pringsheim's ``Fluorescence and Phosphorescence''.
"Phosphorescence", Interscience Publishers
Inc., New York. 1969. Other fluorophores can be found in The Couour Index, 2nd Edition, Volume 2, The American Association of
Textile Chemists and Colorists.1956, 2907
It is described on pages 2923 to 2923. Although only typical fluorescent compounds are listed above, one skilled in the art will appreciate that the present invention is not so limited and that there are many other fluorescent compounds with similar properties. It is well appreciated that compounds are also contemplated for use herein. Preferred fluorescent compounds are described in U.S. Pat.
9,10-bis(phenylethynyl)anthracene, as described in No. 3888786 and is included here for reference. The 9,10-bis(phenylethynyl)anthracene compound considered here is defined as 9,10-bis(phenylethynyl)anthracene or chloro, bromo, fluoro or lower alkyl-substituted bis(phenylethynyl)anthracene. can do. Preferred compounds are selected from 9,10-bis(phenylethynyl)anthracene or chloro-substituted 9,10-bis(phenylethynyl)anthracene. More preferably, the compound is 9,10-bis(phenylethynyl)anthracene, 1-chloro-9,10-bis(phenylethynyl)anthracene or 2-chloro-9,10-bis(phenylethynyl)anthracene. selected from. Examples of 9,10-bis(phenylethynyl)anthracenes that can be used in the present invention are: 9,10-bis(phenylethynyl)anthracene, 1-chloro-9,10-bis( phenylethynyl)anthracene 2-chloro-9,10-bis(phenylethynyl)anthracene, 1,5-dichloro-9,10-bis(phenylethynyl)anthracene, 1,8-dichloro-9,10-bis (phenylethynyl)anthracene, 1-bromo-9,10-bis(phenylethynyl)anthracene, 1-fluoro-9,10-bis(phenylethynyl)anthracene, 1-methyl-9,10-bis(phenylethynyl)anthracene enylethynyl) anthracene, etc. The term "diluent," as used herein, means that it does not render insoluble any of the compounds of formula () or the peroxide component, and that the fluorescent compound is at least partially present therein. is soluble,
Defined as a solvent or vehicle. The phrase "peroxide component" as used herein means a solution of a hydrogen peroxide compound, a hydroperoxide compound, or a peroxide compound in a suitable diluent. The phrase "hydrogen peroxide" includes (1) hydrogen peroxide and (2) compounds that produce hydrogen peroxide. The composition that reacts with the peroxide component to generate chemiluminescence solubilizes the compound of formula () and the fluorescent compound to ^a
10 M, preferably from about 10 ^-3 M to about 1 M ()
and an initial concentration of the fluorescent compound of from 10 ^-5 M to about 10 ^-1 M, preferably from about 10 ^-4 M to 10 ^-2 M, in the reaction system. It may also contain diluents. The diluent should be relatively non-reactive with respect to the compounds of formula (), the fluorescent compound and the peroxide component. Formula () in the composition for reaction with the peroxide component
The concentration of compounds and fluorescent compounds is
about 1.1 to 2.5 of the concentration of the same material in the above reaction system.
The amount is preferably about 1.2 to 1.3 times. Typical diluents or solvents that can be used include esters, ethers, aromatic hydrocarbons, chlorinated aliphatic and aromatic hydrocarbons such as those disclosed in U.S. Pat. No. 3,749,679. . A preferred diluent is dibutyl phthalate. Combinations of solvents may of course be used, but such combinations must not include strongly electron-donating solvents. Hydrogen peroxide is a preferred hydroperoxide and may be used as a solution of hydrogen peroxide in a solvent or as anhydrous hydrogen peroxide compounds such as sodium perborate, sodium peroxide, and the like. Whenever hydrogen peroxide is intended to be used, any suitable compound that produces hydrogen peroxide can be substituted. Diluents that can be used in the peroxide component are relatively non-reactive with respect to hydroperoxides, compounds of formula () and fluorescent compounds, and are diluents such as to be at least 0.01M hydroperoxide. Any fluid that modulates solubility is included. Typical solvents for the hydroperoxide component include water; ethanol;
Alcohols such as tert-butanol or octanol; ethers such as diethyl ether, diamyl ether, tetrahydrofuran, dioxane, dibutyldiethylene glycol, perfluoropropyl ether and 1,2-di-methoxyethane; and ethyl acetate, ethyl benzoate, dimethyl phthalate. , dioctyl phthalate, and propyl formate. Combinations of solvents such as those described above with anisole, tetralin and chlorobenzene may of course also be used, provided that the combination of solvents adjusts the solubility of the hydroperoxide. However, strong electron-donating solvents such as dimethylformamide, dimethylsulfoxide and hexamethylphosphoramide generally cannot be used as the primary diluent for the peroxide component. The preferred diluent for the peroxide component is about 80
It is a mixture of % dimethyl phthalate by volume and about 20% tert-butanol by volume. The hydrogen peroxide concentration in the peroxide component is approximately 0.2M
It can range from up to about 15M. Preferably, the concentration ranges from about 1M to about 2M. The lifetime and intensity of the emitted chemiluminescent light can be adjusted using certain modulating agents, such as: (1) Catalysts that change the rate of reaction of the hydroperoxide with the compound of formula (). will be added. ML is a catalyst for achieving this goal.
Bender. “Chem.Revs.” Vol. 60, p. 53 (1960)
Includes those listed in. Catalysts that alter the rate of reaction or rate of chemiluminescence also include the accelerators of US Pat. No. 3,775,366 and the moderators of US Pat. No. 3,691,085 and US Pat. No. 3,704,231. or (2) by changing the hydroperoxide. Both the type and concentration of hydroperoxide are critical for regulatory purposes. Preferably, a weakly basic accelerator such as sodium salicylate is included in the peroxide component to control the lifetime of the chemiluminescent system. The concentration of the weakly basic accelerator used in the peroxide component is approximately 10 ^-6 M.
from about 10 ^-2 M, preferably from about 10 ^-4 M to about 10 ^-3 M
can be in the range of The initial concentrations of the peroxide components in the reaction system are:
Since the peroxide component contains about 15 to about 60% by weight of the reaction mixture, the concentration in the peroxide component is approximately
It is 0.15 to 0.60 times. The concentration of the hydrogen peroxide compound in the chemiluminescent reaction is at least equal to the molar concentration of the compound of formula (), preferably 1.2 to 5.0 times the concentration of the compound of formula () in the above reaction system. The optimal concentration must be determined experimentally for each particular system. The following examples illustrate the invention.
All parts are parts by weight unless otherwise indicated. Reference Example 1 Production of N-2,4,5-trichlorophenyl-trifluoromethanesulfonamide Trifluoromethanesulfonic anhydride (14.11
g: 0.05 mol) in a stirred solution of 2,4,5-trichloroamine (9.8 g; 0.05 mol) and triethylamine (5.0 g; 0.05 mol) in methylene chloride (5
ml) solution in portions at 0°C under a nitrogen atmosphere. After the addition is complete, the reaction mixture is stirred at 0°C for 1 hour, then heated to 50°C and stirred there for 3 hours. The white solid precipitate is separated by filtration and the liquid is evaporated to give a dark oil. Water (40 ml) is added to the oil and the resulting mixture is extracted three times with diethyl ether (50 ml). The combined ethereal extracts are then dried over anhydrous sodium sulfate, the dried extracts are separated and the separated ethereal solution is evaporated to yield 13.4 g of crude product. Recrystallization of the crude acid product from methylcyclohexane gives the desired product, melting point 104-106°C. Analysis - Calculated _% for _{C7H3Cl3F3NO2S} : C, 25.69; H, 0.92; Cl, 32.11; _F , 17.43; _N , 4.28; _S , 9.79 Actual (%): C, 25.59 ; H, 1.00; Cl, 31.98; F, 17.00; N, 4.28; S, 9.95 Using appropriately substituted anilines and amines in the above method and U.S. Pat. N-(4-chlorophenyl)trifluoromethanesulfonamide, N-(2,4-dichlorophenyl)trifluoromethanesulfonamide, N-(2,4,5-trichlorophenyl)trifluoromethanesulfonamide, N -(2,4,6-trichlorophenyl)trifluoromethanesulfonamide, N-(4-nitrophenyl)trifluoromethanesulfonamide, N-(2-methoxyethyl)trifluoromethanesulfonamide, N-(2-chloro-3 -pyridyl)trifluoromethanesulfonamide, Example 1 N,N'-bis(2,4-dichlorophenyl)-
Production of N,N'-bis(trifluoromethylsulfonyl)oxamide Oxalyl chloride (1.90 g; 0.015 mol) was
-2,4-dichlorophenyltrifluoromethanesulfonamide (5.94 g; 002 mol) and triethylamine (2.0 g; 0.02 mol) were added dropwise to a solution of 1,2-dimethoxyethane (50 ml) at 0°C under a nitrogen atmosphere. Add. After the addition is complete, the reaction mixture is heated to 70°C and held there for 5 hours. The reaction mixture is filtered to remove insoluble materials and the liquid is evaporated to yield 6.05 g (94% of theory) of crude product. Recrystallization of the crude product from cyclohexane gives the desired product with a melting point of 148-150°C. Calculated for C ₁₆ H ₆ N ₂ O ₆ Cl ₄ F ₆ S ₂ : C, 29.95%; H, 0.90%; N, 4.36%; Cl, 22.12%; F, 17.75%; S, 10.00% Measured: C, 30.24%; H, 1.02%; N, 4.24%; Cl, 22.27%; F, 17.19%; S, 10.45% Example 2 N,N'-bis(2,4,5-trichlorophenyl)- Method A for producing N,N'-bis(trifluoromethylsulfonyl)oxamide: Oxalyl chloride (1.27 g; 0.01 mol) is
2,4,5-Trichlorophenyltrifluoromethanesulfonamide (6.2%; 0.02 mol) and triethylamine (2.0 g; 0.02 mol) were added in portions to a stirred solution of methylene chloride (50 ml) at 0°C under a nitrogen atmosphere. Add. After the addition was complete, the reaction mixture was stirred at room temperature for about 4 hours and then filtered to give 2.1
g of crude product are obtained. Recrystallization of the crude product from methylcyclohexane gives the desired product, melting point 190-192°C. Calculated for C ₁₆ H ₄ N ₂ O ₆ Cl ₆ F ₆ S ₆ : C, 27.02%; H, 0.57%; N, 3.94%; Cl, 29.91%; F, 16.04%; S, 9.02% Actual measurement: C, 27.02%; H, 0.63%; N, 3.84%; Cl, 30.06%; F, 16.64%; S, 8.90% The liquid obtained by isolating the crude product was evaporated and the remainder By trituration with water, an additional 3.5 g of crude product are obtained after filtration and drying. The total yield of the second product is the theoretical one.
It is 78.7. Method B Oxalyl chloride (4.44 g; 0.035 mol) was added to N
-2,4,5-trichlorophenyltrifluoromethylsulfonamide (15.0 g; 0.06 mol) and powdered molecular sieve (15 g; Molecular Sieve Type 3A from Union Carbide Co.) in methylene chloride (150 ml). ) into the suspension in portions at 0° C. under a nitrogen atmosphere. After the addition is complete, the reaction mixture is heated to 60° C. and stirred there for 5 hours. The molecular sieve was then separated by filtration and the liquid was concentrated to remove methylene chloride.
g (82% of theory) of crude product are obtained. Recrystallization of the crude product from methylcyclohexane gives the same product as obtained in method A. Example 3 N,N'-bis(4-nitrophenyl)-N,
N′-bis(trifluoromethylsulfonyl)
Production of oxamide Oxalyl chloride (0.825 g; 0.0065 mol) was added to N
-4-Nitrophenyltrifluoromethanesulfonamide (3.61 g; 0.013 mol) and triethylamine (1.3 g; 0.0128 mol) are added dropwise to a stirred solution of dry tetrahydrofuran (40 ml) at 0<0>C under a nitrogen atmosphere. After the addition is complete, the reaction mixture is warmed to room temperature and stirred there for 18 hours. The reaction mixture is then filtered, the solvent is evaporated from the liquid and water (20 ml) is added to the remainder. The resulting precipitate was then filtered to yield 3.29 g (theoretical 92
%) of a crude yellow product is obtained. Recrystallization of the crude product from diethyl ether gives the desired product, melting point 172-175°C. Calculated for C ₁₆ H ₈ N ₄ O ₁₀ F ₆ S ₂ : C, 34.16%; H, 1.42%; N, 9.96%; F, 20.28%; S, 11.39% Actual measurement: C, 34.46%; H, 1.25%; N, 9.80%; F, 19.82%; S, 11.78% Example 4 N,N'-bis(2-methoxyethyl)-N,
N′-bis(trifluoromethylsulfonyl)
Production of oxamide Oxalyl chloride (1.27 g; 0.01 mol) was
A stirred mixture of (2-methoxyethyl)trifluoromethanesulfonamide (4.0 g; 0.02 mol) and triethylamine (2.0 g; 0.02 mol)
- Add portionwise to a solution in dimethoxyethane (40 ml) at 0° C. under a nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred at 0°C for 1 hour, heated to 50°C,
There, the mixture was stirred for 2 hours and concentrated to remove the solvent. Then extract the remaining with diethyl ether and evaporate the ether extract to 4.65g (99% of theory)
A crude product is obtained. Vacuum distillation of the crude product yields a boiling point of 74 at 0.5 mm
A pure product is obtained between 76°C and 76°C. Calculated for C ₁₀ H ₁₄ N ₂ O ₈ F ₆ S ₂ : C, 25.64%; H, 2.99%; N, 5.98% F, 24.36%; S, 13.68% Actual measurement: C, 25.60%, H, 3.11 %; N, 5.77%; F, 23.95%; S, 13.92% Example 5 N,N'-bis(4-chlorophenyl)-N,
N′-bis(trifluoromethylsulfonyl)
Production of oxamide Oxalyl chloride (0.635 g; 0.005 mol) was added to N
A stirred solution of -4-chlorophenyl-trifluoromethanesulfonamide (2.6 g; 0.01 mol) and triethylamine (1.0 g; 0.01 mol)
-To a solution in dimethoxyethane (20 ml) at 0° C. under nitrogen atmosphere. The mixture is stirred at 0°C for 2 hours, heated to 60°C, kept at 60°C for 1 hour and evaporated to give a yellow solid, which is then treated with 20ml of water. Recrystallization of the remaining solid from anhydrous ether gave 2.46 g of the desired product as white crystals, melting at 173-174°C. Yield is 85.8% of theory. Calculated for C ₁₆ H ₈ N ₂ Cl ₂ S ₂ O ₆ F ₆ : C, 33.50%; H, 1.40%; N, 4.88%; Cl, 12.40%; S, 11.17%; F, 19.90% Actual measurement: C, 33.51%; H, 1.38%; N, 4.74%; Cl, 12.10%; S, 11.52%; F, 19.11% Example 6 N,N'-bis(2-chloro-3-pyridyl)-
Production of N,N'-bis(trifluoromethylsulfonyl)oxamide Oxalyl chloride (0.762 g; 0.006 mol) was
- Suspension of (2-chloro-3-pyridyl)trifluoromethanesulfonamide (2.61 g; 0.01 mol) and powdered molecular sieve (5.0 g; molecular sieve type 3A) in methylene chloride (76 ml). Add to the solution dropwise at 0° C. under nitrogen atmosphere. The mixture is then heated to 60°C and held there for 3 hours, then stirred at room temperature for 60 hours. The reaction mixture is filtered and the liquid is evaporated to dryness.
The residue formed is extracted with diethyl ether and the combined ether extracts are dried over anhydrous sodium sulfate. The dried ether extract was then separated and evaporated to 2.33 g (81% of theory).
A crude product is obtained. Recrystallization of the crude product from cyclohexane gives the desired product with a melting point of 104-106°C. Calculated for C ₁₄ H ₆ N ₄ O ₆ Cl ₂ F ₆ S ₂ : C, 29.27%; H, 1.05%; N, 9.76%; Cl, 12.20%; F, 19.86%; S, 11.15% Actual measurement: C, 29.10%; H, 1.14%; N, 9.51%; Cl, 11.95%; F, 19.40%; S, 10.89% Example 7 Chemiluminescence measurement 1-chloro-9,10-bis(phenylethynyl) A solution of anthracene (CBPEA) (7.5 ml) and the reactant under study were mixed in dibutyl phthalate with 2.5 ml of peroxide consisting of hydrogen peroxide and sodium salicylate in 80% dimethyl phthalate-20% tert-butanol by volume. mixed with the ingredients,
A reaction mixture having an initial concentration of 0.38 M hydrogen peroxide, 0.3 x 10 ^-3 M sodium salicylate, 6.75 x 10 ^-3 M CBPEA and the concentrations of the reactants shown in Table 1 is provided, and the chemistry of different systems is Quantitative measurements of luminescence can be made by measuring the intensity of the light emitted at 555 nanometers using a Hirt-Roberts radiometer.
This was done by measuring with a spectrophotometer. The results obtained are summarized in Table 1.

【table】

【table】

Claims (1)

[Claims] 1 The following formula () In the formula, R and R' are independently a C1-C6 alkyl group substituted with a C1-C6 alkoxy group, a phenyl group substituted with a substituent selected from the group consisting of halo and nitro, or a halo A compound represented by is a pyridyl group substituted with. 2 The compound represented by the above formula () is N,
The compound according to claim 1, which is N'-bis(4-chlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. 3 The compound represented by the above formula () is N,
N'-bis(2,4-dichlorophenyl)-N,
The compound according to claim 1, which is N'-bis(trifluoromethylsulfonyl)oxamide. 4 The compound represented by the above formula () is N,
N'-bis(2,4,5-trichlorophenyl)-
N,N'-bis(trifluoromethylsulfonyl)
The compound according to claim 1, which is an oxamide. 5 The compound represented by the above formula () is N,
The compound according to claim 1, which is N'-bis(4-nitrophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. 6 The compound represented by the above formula () is N,
The compound according to claim 1, which is N'-bis(2-methoxyethyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. 7 The compound represented by the above formula () is N,
N'-bis(2-chloro-3-pyridyl)-N,
The compound according to claim 1, which is N'-bis(trifluoromethylsulfonyl)oxamide. 8 (a) The following formula () In the formula, R and R' independently have a carbon number of 1 to 6
An alkyl group having 1 to 6 carbon atoms substituted with alkoxy, a phenyl group substituted with a substituent selected from the group consisting of halo and nitro, or a pyridyl group substituted with halo. (b) a fluorescent organic compound, and (c) a diluent, and these components are present in a ratio and concentration sufficient to produce chemiluminescence when reacted with the peroxide component. A composition that generates chemiluminescence by reacting with a peroxide component. 9 The compound represented by the above formula () is N,
The composition according to claim 8, which is N'-bis(4-chlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. 10 The compound represented by the above formula () is N,
N'-bis(2,4-dichlorophenyl)-N,
The composition according to claim 8, which is N'-bis(trifluoromethylsulfonyl)oxamide. 11 The compound represented by the above formula () is N,
N'-bis(2,4,5-trichlorophenyl)-
N,N'-bis(trifluoromethylsulfonyl)
9. The composition of claim 8, which is an oxamide. 12 The compound represented by the above formula () is N,
The composition according to claim 8, which is N'-bis(4-nitrophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. 13 The compound represented by the above formula () is N,
The composition according to claim 8, which is N'-bis(2-methoxyethyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide. 14 The compound represented by the above formula () is N,
N'-bis(2-chloro-3-pyridyl)-N,
The composition according to claim 8, which is N'-bis(trifluoromethylsulfonyl)oxamide.